Roan Montgomery

Roan Montgomery, born in New Orleans, LA, is a legendary, debonair CIA agent and well-known womanizer who has since passed his prime, and is known to have lived at 1274 S., Palm Canyon Drive, Palm Springs, California, 92264. He is portrayed by John Larroquette.

Roan has a romantic history with General Beckman, and is the first character in the series to have ever called her by her first name, Diane.

Contents

Montgomery is known to have been an instructor late in his career for the CIA, and failed Casey twice in Infiltration and Inducement of Enemy Personnel, or "Seduction School". Roan's favorite drink appears to be a martini.

At a hotel, Chuck is finally assigned to make his move with seducing Banacheck. She was entirely uninterested in him, but Roan had aided him into having a conversation with her, long enough to have her more and more interested. After noticing Chuck had ordered a martini however, Banacheck secretly knew he was being aided by Roan. After Chuck had taken the Cipher from Banacheck's necklace, she captures Sarah and Casey and demanded Chuck or Roan to return the Cipher.

Unfortunately, Roan was no longer the world's greatest spy, he was even deeply refusing to rescue Sarah and Casey, but was inspired by Chuck's determination to save them from Banacheck and her other agents who had pinned them at the Buy More.

After aiding Chuck in ambushing them at the Buy More, Roan is impressed by Chuck's bravery in swinging himself across the roof with a banner all the way to the street, knocking out Banacheck. He then helps Chuck later on in his relationship with Sarah by advising him what to wear, and to give to her, when Chuck visits Sarah at her apartment later for a date.

Roan returns in "Chuck Versus the Seduction Impossible", where Chuck, Sarah, and Casey are sent to rescue him in Marrakech, Morocco. He goes on a rogue mission into bringing down counterfeiter Fatima Tazi, but is captured and in order to crawl himself out of the hole as well as finding out the location of the distribution of her bills, he seduces her.

Later after being rescued, Roan is in Castle before an infuriated Diane Beckman. General Beckman angrily has him benched from the now-permitted mission to bring down Fatima Tazi instead, assigning him to work at the Buy More as a Green shirt. While on his shift break at the Buy More, Chuck consults with him for a relationship advice, as Sarah would prefer to elope for their marriage. Roan shares with Chuck the same problem he has with Beckman throughout decades, telling him that she had wanted to settle down with him, but Roan declines to do so. Roan advises Chuck to create an "erotic atmosphere", where he seduces Sarah into having a family wedding instead, though the plan is thwarted when Sarah does the same method with Chuck by being a belly dancer.

When Casey is hiding in a wall at Fatima's palace, the wall begins to crush down on him when her soldiers were firing against an entire room of the people interested in her counterfeiting bills. Beckman immediately sends in Roan to return to Fatima's palace in Marrakech, where he is to seduce Fatima once again despite how she now knows that Roan was only seducing her to get to her distribution. Chuck calls this as a "Seduction Impossible" as it would practically be sending him to his death.

At Marrakech, as Roan climbs up into Fatima's room, he advises both Chuck and Sarah to never fight with each other and to never go on a mission angry. The two heed his final advice. Afterward, Fatima enters her room, she finds Roan's climbing gear and stealth shirt on a chair. She then looks behind her, finding Roan holding her at gunpoint, already dressed in a white suit and collar. Roan willingly hands her his gun, showing her that he is there just to be with her. Roan explained he had to leave the first time in her castle as there was another woman, his general. Elsewhere, Beckman is monitoring Roan's progress into seducing Fatima to get the location of her entire counterfeit bills. Roan makes a progress long enough to have her tell her motives on collapsing the U.S economy, as they had trembled her village.

After Beckman finally gets the location of her village, where the distribution is, she sends in an air strike. She then calls Roan on his phone, he attempts to answer it but Fatima takes it from him. Beckman addresses herself to her, formally asking who she is currently speaking to. Fatima replies that she is talking to the woman who is about to kill her agent, Beckman instead encourages her and even expresses her relief in finally seeing him die. Fatima sarcastically remarks to Roan that she is apparently another one his fans. After hanging up, another phone interrupts Roan, he answers it and deeply apologizes to her. She thanks him, shortly before she tells him to duck, as she holds up a missile launcher and fires it directly into Fatima's room from a distance, knocking both Roan and Fatima out. When Chuck and Sarah arrive into the room shortly after they rescued Casey, Beckman immediately worries and asks if Roan is still alive. The two help Roan up on his feet, where he simply says "I still got it. Now, where's the bar".

When the mission was over, Beckman is seen at a bar with Roan. The two discuss whether Roan could ever settle down for a normal life with her, but Beckman makes the decision for him instead and finally accepts that Roan is a spy, and that settling down is not meant for him. The two are still pursuing their relationship together, with the lack of settling down.